Azoline derivatives

Abstract

Trifluoromethylbiphenylyl-dihalophenylazolines of formula Iwherein X and Y are, independently fluorine or chlorine, and Z is O or S, their tautomers and salts are disclosed which are useful as pesticides. Compositions of these compounds of these compounds, their use in pesticidal applications, methods of manufacture thereof and intermediates in the manufacturing process are also disclosed.

What is claimed is:  
     
       1. A compound of formula                    
       wherein X and Y are, independently of one another, fluorine or chlorine, and Z is O or S;  
       and where appropriate their possible tautomers, in each case either in free form or in the form of a salt.  
     
     
       2. A compound of formula (I) according to  claim 1 , wherein X and Y are fluorine. 
     
     
       3. A compound of formula (I) according to  claim 1 , wherein Z is O. 
     
     
       4. A method for preparing the compounds of formula (I) according to  claim 1  and where appropriate their tautomers, in each case in free form or in the form of a salt, comprising 
       a) the reaction of a compound of formula                    
       wherein X and Y are as defined for formula (I) and Q is bromine or iodine, with a compound of formula                    
       and 
       b) where appropriate, for preparing a compound of formula (I), wherein Z is S, the reaction of the resulting compound of formula (I), wherein Z is O, with [2,4-bis(methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide] or with phosphorus pentasulfide;  
       and in each case, if so desired, the conversion of a compound of formula (I) obtainable according to the method or by other means, or a tautomer thereof, present in free form or in the form of a salt, into a different compound of formula (I) or a tautomer thereof, the separation of a mixture of isomers obtainable according to the method and isolation of the desired isomers and/or the conversion of a free compound of formula (I) obtainable according to the method, or a tautomer thereof, into a salt, or a salt obtainable according to the method from a compound of formula (I), or a tautomer thereof, into the free compound of formula (I), or a tautomer thereof, or into a different salt.  
     
     
       5. A pesticidal composition comprising at least one compound of formula (I) according to  claim 1  as active ingredient, either in free form or in the form of an agrochemically acceptable salt, and at least one adjuvant. 
     
     
       6. A method for the control of pests comprising applying a composition of  claim 5  to the pests or their habitat. 
     
     
       7. A method according to  claim 6  for the control of insects and members of the order acarina. 
     
     
       8. A method for preparing a composition of  claim 5  which contains at least one adjuvant and comprises the intimate mixing and/or grinding of the active ingredient with the adjuvant(s). 
     
     
       9. A method of protecting a plant propagation material from a pest, comprising treating said propagation material or the cultivation area for said propagation material with a pesticidal composition of  claim 5 . 
     
     
       10. The method of  claim 9  wherein said plant propagation material is treated. 
     
     
       11. A composition to combat ectoparasites or endoparasites in humans or animals, comprising a compound of  claim 1  and a physiologically acceptable adjuvant. 
     
     
       12. The method of  claim 6  wherein said habitat is a plant propagation material or a cultivation area for said plant propagation material. 
     
     
       13. The method of  claim 12  wherein said habitat is a plant propagation material.